tetraethylene glycol bis(acetoacetate) | 7097-93-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: tetraethylene glycol bis(acetoacetate)
• 英文别名: 3,6,9-trioxaundeca-1,11-diyl bis(3-oxobutanoate)；acetoacetic acid 3,6,9-trioxa-undecane-1,11-diyl ester；Butanoic acid, 3-oxo-, oxybis(2,1-ethanediyloxy-2,1-ethanediyl) ester；2-[2-[2-[2-(3-oxobutanoyloxy)ethoxy]ethoxy]ethoxy]ethyl 3-oxobutanoate
• CAS: 7097-93-0
• 化学式: C₁₆H₂₆O₉
• 分子量: 362.377
• InChiKey: GLZCRVUEFBMCJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  467.5±40.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  25
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tetraethylene glycol bis(acetoacetate) 在 [Ru(2,6-Cl2tpp)CO] 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 31.0h， 生成 (15Z)-1,4,7,10,13-pentaoxacycloheptadec-15-ene-14,17-dione
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a
• 作为产物：
  描述：

  双乙烯酮 、 三缩四乙二醇 在 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以86%的产率得到tetraethylene glycol bis(acetoacetate)
  参考文献：
  名称：

  Highly Selective Intra- and Intermolecular Coupling Reactions of Diazo Compounds to Form cis-Alkenes Using a Ruthenium Porphyrin Catalyst

  摘要：

  [Ru(2,6-Cl2TPP)(CO)] catalyzed intramolecular coupling reactions of bisdiazoacetates and intermolecular coupling reactions of monodiazoacetates to afford the coupling products in up to 76% and 93% yields, respectively. Only the cis isomers were obtained from the reactions. Employing such a ruthenium-catalyzed coupling reaction of a diazo compound as a key step allowed the synthesis of Patulolide B in 67% yield with a ratio of >40:1 against its trans isomer.

  DOI：

  10.1021/ol049626a

文献信息

• Synthesis and tuberculostatic activity of podands with a dihydropyrimidine fragment
  作者：E. S. Filatova、O. V. Fedorova、Yu. A. Titova、P. A. Slepukhin、M. A. Kravchenko、S. N. Skornyakov、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-016-1462-4

  日期：2016.5

  toluene was optimized. A multi-component Biginelli reaction was used for the formation of the dihydropyrimidine ring on the ether matrix obtained. Tuberculostatic activity of dihydropyrimidine podands in the in vitro experiments against a laboratory strain H37Rv was studied. A combination of dihydropyrimidine and podand fragments imparts tuberculostatic activity to the compounds obtained, which noticeably

  一种通过加热时用 2,2,6-三甲基-4H-1,3-二恶英-4-one 乙酰乙酰化低聚（乙二醇）制备含 3-氧代丁酸酯的不同聚醚片段长度的 podands 的方法在甲苯中进行了优化。多组分Biginelli反应用于在获得的醚基质上形成二氢嘧啶环。研究了二氢嘧啶荚果在体外实验中对实验室菌株 H37Rv 的抗结核活性。二氢嘧啶和podand片段的组合赋予所获得的化合物抗结核活性，随着氧乙烯间隔物长度的增加，该活性显着​​增强。
• [EN] METHOD FOR PREPARATION OF ACETOACETATE ESTER COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS D'ESTER D'ACÉTOACÉTATE
  申请人：LONZA SOLUTIONS AG

  公开号：WO2021004947A1

  公开（公告）日：2021-01-14

  The invention discloses a method for preparation of acetoacetate ester compounds with amino alcohol catalysts which are themselves diketenized in the course of the diketenization reaction; and subsequent polymerization of these acetoacetate ester compounds with e.g. acrylate compounds to provide resins, whereby the acetoacetylated amino alcohol catalyst partakes in the polymerization reaction.

  该发明揭示了一种利用氨基醇催化剂制备乙酰乙酸酯化合物的方法，这些催化剂在二羰基化反应过程中本身被二羰基化；随后将这些乙酰乙酸酯化合物与丙烯酸酯等化合物聚合，从而提供树脂，其中乙酰化的氨基醇催化剂参与聚合反应。
• Synthesis and structure of functionalized podands containing 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring. Differently substituted dihydropyrimidine podands
  作者：Elena S. Filatova、Olga V. Fedorova、Pavel A. Slepukhin、Gennady L. Rusinov、Valery N. Charushin

  DOI：10.1007/s10593-018-2373-0

  日期：2018.10

  5-а]dihydropyrimidine groups. Byproducts were isolated and identified as podands containing different substituents – one 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring system and a free hydroxy group at the other terminus of the polyether chain. Analogous differently substituted podands, including one 3,4-dihydropyrimidine-2(1H)-thione moiety, were isolated from the reactions of 3-oxobutanoate-containing polyethers with

  在多磷酸存在下，含3-氧代丁酸酯的聚醚与苯甲醛和5-氨基四唑的反应被用于合成含有两个末端四唑并[1,5- α ]二氢嘧啶基团的豆荚。分离出副产物并将其鉴定为含有不同取代基的豆荚-一个4,7-二氢四唑并[1,5- α ]嘧啶环系统和在聚醚链另一端的自由羟基。从含3-氧代丁酸酯的聚醚与苯甲醛和硫脲的反应中分离出类似的不同取代的豆荚，包括一个3,4-二氢嘧啶-2（1 H）-硫酮部分。
• Synthesis of crown ethers containing the 3,5-di(alkoxycarbonyl)pyridine ring system by means of the Hantzsch condensation
  作者：T. J. van Bergen、Richard M. Kellogg

  DOI：10.1039/c39760000964

  日期：——

  The products obtained from reaction of ethyl acetoacetate with several (poly)ethyleneglycols undergo the Hantzsch condensation with ammonium carbonate and formaldehyde giving new crown ethers; transformations and properties of these new compounds are described.

  由乙酰乙酸乙酯与几种（聚）乙二醇反应制得的产物与碳酸铵和甲醛进行汉茨缩合反应，生成新的冠醚。描述了这些新化合物的转化和性质。
• Multicomponent reactions in the synthesis of dihydropyrimidine-containing podands having tuberculostatic activity
  作者：O. V. Fedorova、E. S. Filatova、Yu. A. Titova、M. A. Kravchenko、I. D. Medvinskiy、G. L. Rusinov、V. N. Charushin

  DOI：10.1007/s11172-018-2131-6

  日期：2018.4

  2-thienyl substituents have been synthesized via the multicomponent Biginelli reaction. Tuberculostatic activity of the novel podands was shown to depend on the polyether unit length. In particular, activity of dihydropyrimidinethione podands against laboratory strains of Mycobacterium tuberculosis, H37Rv, M. avium, M. terrae, and the clinical strain of multi-drug resistant M. tuberculosis (MDR), increases

  二氢嘧啶硫酮 podands 以及含有 2-噻吩基取代基的 podands 已通过多组分 Biginelli 反应合成。新型 podands 的抗结核活性被证明取决于聚醚单元长度。特别是，二氢嘧啶硫酮 podands 对结核分枝杆菌、H37Rv、鸟分枝杆菌、土地分枝杆菌的实验室菌株和耐多药结核分枝杆菌 (MDR) 的临床菌株的活性随着聚醚单元长度的缩短而增加。